The outlined research project—titled “A gradual transition: Perestroika, opposition, secession and transformation in Estonia in the light of the border-crossing elite networks from the mid-1980s to the early 1990s“—focuses on the interplay between representatives of the Estonian exile in Western Europe and North America and oppositional circles in Soviet Estonia in a longue durée perspective, which stretches from the beginnings of perestroika to the first years of independence. Challenging the narratives of classical political and diplomatic history and the focus on ‘ruptures‘ that characterizes the discourse on the Central and Eastern European revolutions of 1989 and the demise of the Soviet Union two years later, this project stresses continuities that integrate these historical milestones into a broader context. Focusing on a perspective from below that draws special attention to the informal networking process on the societal level, which anticipated the lively cooperation between diaspora and home country in the post-Communist 1990s, Soviet Estonia’s transformation will be presented as a continuous process of change from the mid-1980s onwards. The country’s ‘re-Westernization’ began far earlier than with the onset of national independence and with considerable participation of ‘the West’. A rising level of freedom of travel and communication enabled the Soviet Estonian opposition to interact with the Western exile, leading to fruitful consultations in the transition process and a cooperation that coordinated the political struggle of exile and homeland for the sake of a free Estonia. These elite networks across the Iron Curtain are seen as the basis of the close cooperation between Estonians at home and abroad, which to a considerable extent characterizes Estonia’s politics, business, science and culture still today.